


Double Dates

by ForTheLoveOfChuck



Category: Supernatural
Genre: M/M
Language: English
Status: Completed
Published: 2015-03-04
Updated: 2015-03-04
Packaged: 2018-03-16 07:42:07
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 2,161
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3479999
Author URL: https://archiveofourown.org/users/ForTheLoveOfChuck/pseuds/ForTheLoveOfChuck
Summary: <blockquote class="userstuff">
              <p>Sam/Gabriel and Dean/Cas going on a double date.</p>
            </blockquote>





	1. Two nervous angels, two new outfits, and one new plan.

**Author's Note:**

> I am going to try my best to make it easy to follow.... sorry if it doesn't work out. let me know and I can maybe reword it.  
> Also, this is not necessarily canonverse... a lot of the ways they talk doesn't line up with how the character would.... sorry guys. I'm still working on getting the hang of writing fanfiction...

"I still don't understand why I can't wear my normal clothes for this Gabriel." Says a disgruntled Castiel. He and his brother have been trying on different outfits for the last half hour.

"Calm down Bro! We have to look good if you want these two boys to say yes! You don't understand; you've had sex,  **once**. Take it from me, and just get changed back into your other clothes." Gabriel chastises his younger brother. He has been waiting for this day for a very long time. They take the clothes to the register, pay, and leave.

 

* * *

"Come on, Sammy. Rise and shine. We're going hunting for pie!" Dean shouts over the radio blasting between them. He's been up for a while, gotten showered and dressed, lacing his boots he glares over at his lump of a brother Sam. 

 

"I don't wanna get up. Get your pie yourself." Sam mumbles and throws his pillow at Dean with terrible aim, hitting a lamp on the other side of Dean's bed.

 

"Whatever you say Rapunzel; I'm not getting your coffee for you though." Dean says and walks over to the door. Laughing at Sam's continuing to throw things. "Maybe if you got up, your aim would improve."

 

"I'm up, I'm up! Just give me 5 minutes." Sam says, scrambling out of bed and into his jeans. 

 

"Knew the coffee would get you going." Dean chuckles, heading out the door to wait in the Impala. "I'll be in the car." He shouts back.

 

* * *

"Are you sure? Why do I have to do it? What do I ask?" Castiel asks his brother. He's been put on location duty.

 

"Just call and ask Your boy-toy where they are. Say you wanted to meet up and talk about a possible case. He's Dean, he won't say no to you." Gabe tries to convince his brother. "and keep your voice low, or he'll know something's up."

 

* * *

"Yeah, Cas?" Dean's a bit surprised, he hasn't talked to Castiel in a month, "What you need?"

 

"Umm... I've got a possible case." Cas explains in a voice like Misha's in pitch, "Tell me where you are and we can meet up." Cas' voice shifts back down to normal after a short cough.

 

"You alright, man? You seem a bit nervous. Everything okay?" Dean asks, vaguely concerned.

 

"Yes, fine Dean. Just nervous about the case. Where are you?" Castiel improvises.

 

"Janelle's diner in Byron, Michigan. Just sat down. See you soon." Dean answers and hangs up.

 

"Okay, see you soon Dean." Castiel says to open space as he removes the phone from his ear. 

 

* * *

"What did he say? Did you find out where they are?" Gabriel asks, more hysterical by the minute.

 

"Yes Gabriel, now we should probably get dressed if we are going through with this ridiculous plan of yours." Cas answers, heading to the wardrobe to grab the new outfit he bought for this meeting. He also has a new suit for the actual date.

 

"Probably." Gabriel says as he changes into the brand new jeans he bought so they would blend in with the Winchesters. He jumps into his new shoes and helps Cas untangle himself from his new jacket. "You are one casual son of a bitch." 

 

 

 

 


	2. Execution is a must

**Summary for the Chapter:**

> Castiel and Gabriel somehow manage to stumble through the "asking out"

**Notes for the Chapter:**

> Thanks for your comments and kudos!! It helps me to get a better feel of what to make this... :) Hope you like it.

"Are you sure about this? I'm sure we could find another way." Cas sulks as he and Gabe prepare to leave.

"Yes, I'm sure. You want to date Dean, don't you?" Gabriel chastises back.

"Of course I do. I just don't think this is the best way." Cas says, worry evident.

"We'll be fine. Let's go." Gabriel reassures, and they disappear just to show up in a small village town called Byron.

* * *

"Hey Cas!...Gabriel... why's he here? And why are you dressed like that?" Dean asks, appraising the new 'casual' clothes Cas is wearing. **  
**

"We'll tell you inside. Can we go in now?" Cas asks, strained.

"Sure, yeah, Sam's already got a booth. Hopefully it's big enough for all four of us." Dean answers, curiously.

* * *

"Hey Sam. I hope you don't mind I brought Gabriel along..." Cas says as he slides into the booth across from the brothers. **  
**

"No, no problem. So why did you want to meet?" Sam asks, surprised, pleased?

"Well, that's the thing. Let's cut to the quick there Sammy. I like you, and Cas here likes Dean. We propose a double date for tonight." Gabriel rushes out before he loses his nerve.

"So, no case?" Sam asks, shifting uncomfortably.

"Well, we found a case as back up in case we didn't follow through with our plan." Cas blurts out, receiving a hearty glare from Gabriel.

 **  
** "Oh. Okay. Can we umm, have a minute guys?" Dean asks gruffly, and promptly gets up grabbing at Sam's sleeve to take him with him. "Be right back."

* * *

"Do you want to do this Sam? Cause if you don't, we won't. No questions asked." Dean gruffly asks Sam, trying to avoid pulling the restaurant's attention. Not an easy task when you're lugging a 6 foot 4 inch man around.

 

"I don't mind; and obviously you want to. I mean look at them. Cas bought a pair of jeans. He wants to be with you. And.... Gabriel isn't all that bad... not once you get to know him." Sam tells his brother seriously. It's fairly obvious that they both want to.

 

"Alright, you tell 'em or should I?" Dean asks with a laugh.

 

"I'll do it. I'm gonna play hard to get." Sam answers with a wink. "What? I've never done it before!" Sam demands when he sees his brother roll his eyes.

 

"Nothin Sammy. You do this however you want." Dean chuckles and heads back his seat as his brother follows him.

 

* * *

 "Hey guys. So we came to a decision. But it depends on you. It depends on how serious you two are. You are going to have to prove you want to date us. We ain't just free pieces of ass." Sam explains, and chuckles at his small joke at the end. "Let's go. We're done eating." Sam says as they walk out. 

 

"Umm.. okay. What can we do to prove it?" Gabriel asks timidly. Becoming more insecure by the minute.

 

"Well, first, you're gonna have to show us where you bought these fantastic jeans. They make your ass look great!" Sam chuckles, and slaps Gabriel's behind. All 3 others all look at Sam like he's grown another head. "What? Never seen a man look good in jeans before?" He chuffs back at them.

 

"Well, okay then Sammy. If that's how you wanna play it." Snarks Gabriel as he teleports them all to a naked beach in Vancouver. 

 

"Oh. My. God. That is NOT what I wanted! Take us back now Gabe. Or take us to the shop you bought the jeans from." Sam freaks. covering his eyes and trying his best not to laugh.

 

"Fine." Gabriel snaps and they all fall to the floor of a rue 21 somewhere in Flint, Michigan. Surprisingly only about 30 miles away from the place they all met.

 

"Wait. You bought those jeans here?" Dean asks while oogling Cas' butt.

 

"Yeah, you like?" Cas taunts, finally gaining his courage again.

 

"Hell yeah, I like." Dean chides back. Huge grin on his face. When Sam looks his way all he can do is wink back.

* * *

 

"I did as you asked. Can you just give us a straight answer already?" Gabriel whines unashamed.

 

"Dean?" Sam gives his brother a look giving him the floor.

 

"Yes guys. We'll go out with you." Dean answers. "Sammy here just wanted to rile you up."

 

* * *

 

"Okay. See you at 7:30!" Cas yells back as they drop the boys back at Janelle's and leave to get ready for their date. 


	3. Awkward makes for great conversation

**Summary for the Chapter:**

> The actual date commences... and there are spilt drinks... plural... this shall be interesting...

**Notes for the Chapter:**

> Once again. thanks for the feedback! it really helps... Hope you like it. and you can always comment prompts for my future works if you like...

"Dude, what are you wearing? You look like a butler." Dean asks his brother and breaks into a fit of giggles. yes, hysterical giggles. Dean is way more nervous than he expects.

 

"It's my 'interview' suit. no vest?" Sam answers, gazing into the mirror. 

 

"No vest. Damn, look at us Sammy. Acting like a bunch of giddy teenage girls. What the hell?" Dean says shaking his head.

 

"Yeah, I know. Where do you think they're taking us? Knowing Gabriel; it'll be good. Damn, this is certainly not anything I  **ever** expected us to be doing. Especially together." Sam asks, curious and filled with odd laughter. 

 

"Well, the world is a strange place Sammy. A strange place." Dean laughs, shaking his head. For the moment, the world is off of his shoulders.

 

* * *

 

"Come on Castiel. You have to wear it. Or we will be late. It's already 7:15." Gabriel chastises as he tries to chase Cas into his new baby blue suit.

 

"I feel like a cherub. Dean isn't going to like this on me. Maybe I should just stay behind." Cas cries as he sits down in the suit that matches his eyes.

 

"Dean is going to love you; Clothes or not. Come on little brother. It's time to go." Gabriel states softly as he pulls a relenting cas off of his bed and snaps them to Sam and Dean's motel. 

* * *

 "Hey boys, ready to go?" Gabriel asks when Dean answers the door. "Cas is waiting by the car... he's a little self-concious. He doesn't think you'll like what he's wearing... can you help him out?" he tells Dean when he sees his eyes looking for his angel of choice.

 

"Oh yeah... umm... great.. yeah. I'll, I'll go.... Thanks Gabriel. Sam's the same way." Dean stutters as he walks to the car to comfort Castiel.

 

"Hey Sam, how are you tonight? You look mighty fine. Here let me get that for you." Gabriel reaches to tie Sam's bowtie for him, but Sam stops him so he can just soak in the Gabriel hotness. 

 

"Hey, thanks. You umm... you look really nice tonight Gabriel. When did you get this suit?" Sam asks while he checks Gabe out. Gabriel is wearing an olive green blazer with brown dress pants that do wonders for his eyes.

 

"Oh this old thing? Had it for ages!" He says as he waves it off. "I think I bought this the first time I met you Sam. It matched your eyes."

 

* * *

"Cas... Where are you?" Dean shouts into the dusk.

 

"I'm over here... don't look at me Dean... I look stupid!" Cas says as he huddles in a tree nearby.

 

"Come down. it can't possibly be worse that Sammy earlier. Suit and a sweatervest.... no go.. just come down... you'll have to let me see eventually." Dean chides, and stands starstruck as Cas stands in front of him. 

 

"Where the hell did you get the notion that I wouldn't like this? You look fucking fantastic. You look like Bon Jovi sounds. Whole hell of a lot better than me. I'm wearing a cheap-ass suit that I wear to interview witnesses." Dean can't stop talking once he starts, and Cas has to stop him with a simple kiss. nothing heavy. just a sweet kiss on the cheek.

 

"You look fine to me Dean." Cas chuckles and leads Dean back to the hotel doorway so they can tell the other two they are ready to go.

 

"Be out in five. Now I have to redo his hair. and his bowtie." Gabriel calls out; so Cas and Dean wait in the car for them to be ready to go.

 

* * *

 

"Table for four please, reserved under Winchester." Cas tells the hostess as they walk into the town jewel, Lucky's, in Owosso Michigan. 

 

"Fantastic. Right this way." The hostess says enthusiastically as she shows them to their seats. 

 

"four beers, two of your best cheeseburgers, a ceaser salad, and an order of nachos.  oh and, four slices of today's pie. thanks."Dean orders for all of them as the waitress comes around. "I feel we're a bit overdressed... but hey, a good looking group of men never goes out of style." 20 minutes and two beers later, their food finally comes. Cas and Gabriel reach their hands out to do the blessing, and in the process manage to spill what remains of Cas' beer across the table. 

 

"SHIT. So sorry, I didn't mean to.... I'm really sorry..." Cas gasps while he tries to grab as many napkins as possible; they are all scrambling to mop up the mess and no drinks still stand but Dean's.... lucky for him; it was empty. 

 

"Can we get this to go?" Dean asks as he sends the nearest waitress off to do his bidding. "Maybe we should take you home... You need to get out of these clothes. They're soaked!" 

 

"Better idea. You take Cas to your room. I'll take Sammy here to mine. Win, Win.. Told you he'd love you clothes on or off there Cassie!" Gabriel says with a wink as he puts his hand on Sam's shoulder, transporting him to his hotel room.

 

* * *

The rest is left better to your imagination. ;)

 

**Notes for the Chapter:**

> sorry for the suggestive stuff and the swearing... whoops... hope you liked it :)

**Author's Note:**

> Again.... sorry if this doesn't work... just let me know so I can fix it...


End file.
